methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside

Base Information

• Chemical Name: methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside
• CAS No.: 134296-61-0
• Molecular Formula: C₄₂H₅₀O₁₅
• Molecular Weight: 794.85

Synonyms:methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside

Chemical Property of methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside

Chemical Property:

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Technology Process of methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside

There total 12 articles about methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

→ methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside (134296-61-0)

Guidance literature:

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 - 20 ℃; Molecular sieve; Inert atmosphere;

Reference yield: 84.0%

methyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside (19488-49-4) + 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl 1-piperidinecarbodithioate (134296-53-0) → methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside (134296-61-0)

Guidance literature:

With 2,6-di-tert-butyl-pyridine; methyl trifluoromethanesulfonate; In dichloromethane; for 1.5h; Ambient temperature;

DOI:10.1016/0008-6215(91)84154-7

Reference yield: 55.0%

methyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside (19488-49-4) + 1,1,3,3-tetramethyl-2-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)uronium triflate → methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside (134296-61-0)

Guidance literature:

With 3 A molecular sieve; In dichloromethane;

DOI:10.1016/0008-6215(92)80067-B

upstream raw materials:

methyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside

2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl 1-piperidinecarbodithioate

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Downstream raw materials:

methyl 2,3,6-tri-O-benzyl-4-O-α-D-mannopyranosyl-α-D-mannopyranoside

(2S,3R,4S,5R,6R)-2-((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

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